Key West Festival to Salute Repeal of Prohibition Dec. 3-5

KEY WEST, Fla., Nov. 5, 2026 — Rumrunners, renegades, bootleggers and flappers can celebrate the repeal of Prohibition, the 1920-1933 U.S. ban on alcoholic beverages, at a free-spirited Key West festival that also commemorates the birth of Sloppy Joe's Bar.

The End of Prohibition Celebration is set for Thursday through Saturday, Dec. 3-5, at the landmark Sloppy Joe's at 201 Duval St. Planned festivities include Prohibition-era film showings, nonstop live music, 1920s costuming, a themed "true crime tour "of Key West, mixology demonstrations and an epic party taking place Dec. 5 — the 93rd anniversary of the adoption of the U.S. constitutional amendment that ended Prohibition.

Sloppy Joe's is a fitting location for the celebration, since original owner Joe Russell was one of the daring Florida Keys rumrunners who imported contraband liquor from Cuba during Prohibition's so-called "dry" years. He also operated an illegal speakeasy for thirsty patrons who, according to local lore, included author and 1930s Key West resident Ernest Hemingway.

On the day Prohibition was repealed in 1933, Russell proudly opened his bar as a legal establishment. Hemingway, a close friend of Russell's, frequented Sloppy Joe's until he left Key West in late 1939.

As well as live entertainment from 10 a.m. to 2 a.m. daily at Sloppy Joe's, the End of Prohibition Celebration features several themed events — beginning Thursday, Dec. 3, with a salute to the third "birthday" of Sloppy Joe's Blonde Reserve Rum. Attendees can enjoy Prohibition Punch featuring the signature rum, learn to make the unique libation, and spin the Wheel of Fun to benefit the Sloppy Joe's Foundation that provides grants to local nonprofits.

On Friday, Dec. 4, the Hemingway Rum Company at 201 Simonton St. will offer a VIP tour of its Papa's Pilar Distillery, founded by the late author's family. Attendees can anticipate little-known revelations about Key West's rumrunners, as well as insights into rum's history and influence.

Throughout the festival, elements will reflect the cultural shift that characterized the era called the Jazz Age or "Roaring 20s." They include the explosive rise of jazz and ragtime music, dance crazes like the Charleston, and the "flapper" movement that heralded greater independence for women.

Anti-Prohibition revelers can party like it's 1933 during Sloppy Joe's Repeal Party, the highlight event set for Saturday. Attendees are encouraged to wear shimmering flapper dresses, snazzy fedoras, and other "Roaring 20s" garb to compete for prizes in the Flamboyant Flapper and Gentleman Gangster costume contest.

Other attractions include mixology presentations, a selfie station with 1920s accessories available to "jazz up" patrons' photos, an appearance by a vintage Anheuser-Busch delivery truck, prize giveaways and period cocktails. At 5:32 p.m. — the moment in 1933 when the repeal became official — "Joe Russell" will appear to announce Prohibition's end and the birth of Sloppy Joe's.

For event information, schedule and ticketing links, visit Keywestbootleggers.com.

Media Contact: Carol Shaughnessy
Phone: 305-797-0579
E-mail: [email protected]

SOURCE Sloppy Joe's Bar